You Chose Poorly is a 14-episode podcast about tech products and self reflection. It’s selfish and self-serving, but it asks questions everyone should ask from time to time: am I doing right by the people around me, and am I spending my time and money in ways that push me forward?

Because of that, You Chose Poorly is maybe the most inward-facing project I’ve done. I don’t talk about myself much on International Object or Fran’s Not Here. I don’t use my own life as inspiration in my novels. I usually try to get out of my head for creative work. But You Chose Poorly felt like a very specific form of (very first world) therapy.

I had a great co-host. Mikey Llorin is funny, observant, and was willing to push me with insights I hadn’t considered. If I had done this podcast with anyone else, it wouldn’t have been as good. He and his wife just had their first baby, and I’m really happy for them.

We did 14 episodes, which makes it short enough for me to actually run down everything we talked about in a blog post. It makes for a cool snapshot of technologies that have been on my mind most of my adult life (and some of my childhood).

In the first episode, we discussed a small handful of iPods, what they meant in their lives, why certain models were chosen over others, and what the iPod meant in the 2000s before ubiquitous internet music streaming.

Then, we hit on iPads, which became a running device to touch on throughout the show. This was definitely Mikey’s linchpin product, and we talked about how it’s almost impossible to pick the “right” one, even if they’re all pretty great.

Third, The Palm Pre, Palm’s last phone before going under. I still blame myself for this product dying, so we broke open the beautiful and troubled little pebble that effectively killed Palm. Also discussed: Palm Pilots, Apple lifting features from the Prē, and if there’s anything to learn from Palm’s demise.

Returning to apple for episode 4, we discussed their services, quarterly results, my iPhone 6, Apple Music, iTunes Match, Zune Pass, and whether or not it is a poor choice to put all your stuff into iCloud (spoiler: probably).

In episode 5 we talked video games, namely, my first video game system: The TurboGrafx-16. We talk about other systems as well, the idea of a “system,” and how choosing well in gaming is still tough.

Episode 6 is the Rdio episode, and streaming music. Topics: What happens when you fall in love with a failing music service? What do you tell the people who signed up due to your evangelism? What happens when the boat sinks?

Episode 7 and episode 8 were dedicated to talking about the incredible mess (and the incredible mess I keep myself in) of messaging apps. It’s a problem that still frustrates me. Full disclosure: Skype is back on the home screen. Frick.

In episode 9 we talked about Keynotes. While not a “product,” they’ve still become something to consume and enjoy in their own right. We ask: Is it a waste of time for a regular consumer? What is it about nerdy drama that keeps us coming back? And is it about the products, the people, or the (once again) weird feeling of unearned superiority from knowing stuff faster than other people?

Episode 10: Workflows. Is trying to get everyone on board with new workflows always a mistake? Do you just drive yourself nuts knowing the future is right there, just out of reach, while everyone else around you is fine just faxing stuff? We tried to unpack an issue that plagues early adopters and automation enthusiasts.

It took us a while but we finally got around to talking about Photos in episode 11. In it, I tell a story about recommending a service that recently shut down, and this opens the lens for a larger discussion: Photos. What do you do with them? How do you trust they’ll still be there if you want to see them later? How much money do you have to throw at this problem? And can there just be one place where they live (tldr: no).

In what I consider a sister episode to the Photos episode, episode 12 is about reading digitally. In this day and age, what’s the best way to read a book? Mikey and I try to figure out why “use an ebook reader” isn’t automatically the answer. We also talk about the ebook readers we’ve owned, and if any of them were wrong.

Episode 13 returns us to gaming with the big craze of summer 2016: Pokemon Go. Discussed: the wisdom of avoiding never-ending video games, and how good the game might be for society. Also, a little bit of iOS 10 Beta chat.

Finally, our season finale episode. Mikey and I cap off the first season of You Chose Poorly by talking about what comes first (hint: it’s people, not products), the impossibility of buying the right camera, and when you have to turn off the “product hunt” and just deal with what you’ve got.

Somehow, through all of that, we didn’t get to the Zune. Well, we have to leave something for season 2.

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